For young adults entering college, social pressures can exert significant psychological stress. For Caribbean nationals, these challenges can be exacerbated by experiences with the U.S. racial binary framed by the rule of hypodescent --the one drop rule. Using testimonio as method and borrowing elements of critical autoethnography, I delve into one aspect of the transcultural experience of Caribbean nationals studying in the United States by exploring and reflecting on one participant's perspectives on race and whiteness. I present this participant's perspectives and follow with an examination of my own ways of knowing in order to highlight the questioning and internal conflict that emerged as a result of these conversations on whiteness.